


The Gang Gets A New Waitress

by Duckyy



Category: It's Always Sunny in Philadelphia
Genre: F/M, Multi
Language: English
Status: Completed
Published: 2020-01-16
Updated: 2020-03-16
Packaged: 2021-02-27 04:53:27
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 13,023
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22281394
Author URL: https://archiveofourown.org/users/Duckyy/pseuds/Duckyy
Summary: Reader finds her neighbor Charlie Kelly asleep in the building hallway and lets him crash on her couch. After losing her old job she joins The Gang working at the bar, and when Dennis is rejected he swears he will have her. Mac and Dee bet on who will win y/n.
Relationships: Charlie Kelly/Reader
Comments: 22
Kudos: 73





	1. Meeting Charlie

After a long night of working at a bar filled with blurry faces who didn’t tip well (if at all) and training a waitress who couldn't get off her phone, y/n was done with the world after picking up a few necessities and groceries. She just wanted to eat dinner, get in bed and ignore the screaming cats outside.

She really hadn’t met many of her neighbors and preferred to keep it that way, as she didn’t want to put names and faces to the yelling heard late at night arguing about god knows what. And she was only staying there because that's all I could afford, not the charming neighbors.

Though she had met a cute guy who worked at a bar she went to every once and a while with friends, it was close and the beer was cheap. He was scruffy and probably gay, or somehow unavailable. She definitely had a type. He kept to himself mostly and she only heard him every once in a while through the walls singing love songs about men.

She stepped on some crushed and crumpled newspapers that were scattered along the hallway and cursed her litterbug neighbors and she began searching through her purse when she tripped over a man laying in front of what she assumed was his apartment door.

“Agh-” she pressed her hand against the wall to stop herself from completely crushing him. He barely woke up, almost like he was on some kind of drug, and one glance in his red eyes confirmed my suspicion that he was on something or had been crying like he had been dumped right before senior prom and his date went with his best friend instead. Not like she had any experience with that. “Charlie?”

He groaned and started to push himself up and glaring at her, though it was hard to be intimidated by him as he looked like a kindergartner had been left alone at home and aged 40 years. She stood up and picked up the groceries that had fallen with her before offering him her hand.

“Sorry buddy, boyfriend lock you out?” he eyed her hand suspiciously before taking it, seemingly surprised when she started to pull him up. “Uh no, my roommate/maybe father kicked me out so he could bang a prostitute, so my night is so much better being crushed by a weird lady”

She raised her eyebrows, choosing not to process everything he said but getting the gist “Oh- uh well if I were you I wouldn’t sleep here on the floor, it’s not exactly clean and you might get stabbed while you sleep” He groaned and leaned against the wall, “Ah I’ll be fine I’ve done this tons of times, might get bit a few times but it won't wake me up.” 

She looked him up and down and cleared her throat, “Um ok... Well if you want you can crash on my couch instead of the hallway floor, it’ll be cleaner and probably warmer. Plus,” She said, shaking her grocery bags “I’m making spaghetti” 

He seemed to perk up with that and nodded his head, “Uh yeah sure dude, are you sure you want to let a stranger into your apartment?” She shrugged, “You look like you could use a pick me up, and I've seen you around enough to know where you work, as long as you don’t try to murder me, we should be fine. Can you carry these bags while I unlock the door?”

He nodded and took the bags and she opened her door, “Come on in,” She said, holding the door open for him and he stepped in, the apartment was mostly clean with a little kitchen and a small worn-out loveseat, and a queen bed in the corner covered in blankets and pillows.

She took the bag from him and put it on the counter before putting stuff away. He closed and locked the door behind him, looking around “Wow, compared to you my apartment is pretty shitty” She laughed and shook her head, “Nah this place is so cramped I can never have anyone over, can’t imagine having to share this space with a roommate.” He sat down on the loveseat and nodded, “Yeah we share a bed but we agree on a lot, except for when he kicks me out to bang one of his ladies”

She started dinner and listened to him ramble on about his friends, movies, his crush The Waitress, which made her a little confused about how many times she could have sworn he was singing to a man and how she had only really seen him with men and a woman he completely ignored. And of course how he loved going down the sewer with his roommate Frank and looking around for treasure.

“There’s always something cool down there, I mean the walls of water are scary but as long as you take off your clothes and hold it over your head, you should be fine” At that point, she wasn’t sure if he was telling her how to go down the sewer and navigate the city or telling a story. 

“Hey why don’t you like just wear rain boots and like rubber suits?” he just stared before carrying on his own, muttering a simple “Oh, that makes sense” but she wasn’t completely sure he knew what she was saying or just pretending to, but it was just nice to have company so she just went along with it and let him continue.

“So me and Mac thought everyone had turned into zombies but it turned out they had been drugged with the milk.” She pulled out two bowls, “Dinners ready Charlie” She filled his bowl up and gave him a fork to eat with, but he just cast it aside and ate it with his hands, before continuing to talk with his mouth full. “Thanks, this reminds me of the time Dee asked if I wanted to go to a spaghetti day” 

They ate dinner, she was just silently listening to Charlie rambling on about his stories again till they were done and she was washing their dishes. “Hey Charlie, there are towels in the bathroom if you want to shower before bed.” He nodded and went to the bathroom as she cleaned up the dinner mess and pulled a blanket and pillow from her bed, making a small makeshift bed on the loveseat.

He came out of the bathroom, steam slipping into the room and a raggedy white towel wrapped around his waist. “Hey, thanks for everything but this isn’t one of those things where you're doing this all so I’ll bang you right? Cause I have a friend who does that kind of thing and I don’t want you to think I’m like a prostitute.” 

She started to laugh, unable to help it, “No Charlie, I’m just being nice I don’t expect you to sleep with me because I made you dinner and I’m letting you sleep here.” He smiled, “Well, I owe you one so if that’s what you want I’d be down y’know, just say the word” Her cheeks felt hot and she looked away, “Sorry Charlie, you’ll have to buy me dinner first, but I appreciate the gesture”

He smiled, and she reached over and kissed his cheek quickly, making his cheeks flush pink and an obvious confusion in his face like he wasn't used to any physical interaction. “Goodnight,” she said, heading into the bathroom and changing into a T-Shirt and Shorts. By the time she got back, he was passed out, sleeping in a ball. She climbed into bed and put in her earplugs, having no clue how he fell asleep so fast with those damned cats yowling outside. 

But then again, he did smell like cat food, so maybe the cats outside were his.


	2. Meeting The Gang

The next morning was cold and y/n was awake before Charlie. He was passed out on the couch, dead to the world and she checked the time, it was seven and she had to get to work in an hour for the brunch rush.

People were always in a rush for a weird fancy meal. She hurried to take a hot shower to warm up and get dressed in the usual uniform, white button-down, and black slacks. She threw a sweater on and snatched her purse. She made some oatmeal for breakfast and left him some on the stove and a note.

“Thanks for the company, breakfast is served, lock the door behind you and I’ll see you at the bar” and she was out of there, she was in a hurry and it's not like she had anything worth stealing. Charlie woke up confused when he heard the door slam.

He stretched on the couch and groaned when he heard a knocking at the door, “Charlie? Are yah in there? My whore is gone. I've been knocking on everyone's door and," he laughed "They haven't been happy to hear my stories" Charlie stood up and scratched his back, coughing before speaking.

“Yeah Frank hold on.” He walked over to the door and opened up the door before he saw the sticky note on the counter and let Frank in “Ooh this chick your seeing sure has a nice place, you’d better trap her and live a life of luxury” he ignored most of what he said when he finally saw it. 

“Hey, Frank can you read this to me?” He hummed and walked over, taking the note “The broad made you breakfast and asked you to lock her door, AND she’ll be at the bar tonight so the gang can see her for ourselves.” he said, wiggling his eyebrows at that.

Charlie made his way to the stove and hummed, “Ehhh I don’t know Frank I think she’s into me and when I offered to bang her she just said goodnight, but she did kiss me cause ya know I'm sexy. You’re the crooked businessman dude, you think she’s scamming me like those berries Dee and I tried to sell?” 

Frank looked around, “This place is nice but she still lives in the same dump we do, and all this stuff is cheap so I don’t think she’s got money so there's nothing we can get from her, except a place for you to stay while I’m seeing my whores”

Charlie cringed and leaned on the counter eating the oatmeal straight from the pot, using the spoon to express his thoughts while he talked, scattered and rapidly waving the spoon while eating “Yeah well she’s not a bad cook, even though I would have preferred a nice milk steak but she did do it for free” 

Frank nodded, “Well come on, let’s get to the bar and see what the gangs up to, maybe we can make some quick cash and you can take the girl out so you can keep her around” Charlie shrugged and put the pot back on the stove before following Frank, making sure to lock the door behind him.

“I don’t know Frank, I’m a one waitress man” Frank looked at Charlie, confused. “You're telling me your new lady is a waitress too? I swear Charlie I don’t know why you’re so obsessed with people who serve food.”

Charlie scoffed, “Well why do you love prostitutes?” Frank laughed, “Your mother was one.” and Charlie groaned and glared at him as they made their way to Frank's car. The whole car ride was filled with talking about Charlie’s mom. When they were walking in he was clearly frustrated.

“No you don’t understand dude, they were just cheering my mom up and nothing else-” He stopped dead in his tracks when he saw Dennis flirting with y/n at the bar. She looked over and raised her beer to him “Heyyy, did you lock the door?” she slurred, not as good at drinking as The Gang. he nodded before slowly approaching her. “Hey, what are you doing here so early y/n?”

She sighed and looked down, “Lost my job, the boss fired me to hire on his bimbo girlfriend, turns out the girl I was training wasn’t my coworker's replacement, she was MY replacement.” she took a quick swig from the bottle.

“Needed a cheap drink fast, so here I am.” She said and turned to the dude who had obviously trying to get into her pants “You wouldn’t happen to be needing a new waitress would you?” Suddenly, a blonde woman burst out of the bathroom “Yes! We need a new waitress, the bars have been super busy lately and It’s getting too much with you guys sitting back doing nothing.”

“Dee, you bird bitch, we need to vote before making these decisions and you know that just because your telling bad jokes to the customers doesn’t mean you're doing more than us.” Dee scoffed, “Well Dennis, I need help and having her here will keep things working. I vote to have her work here” 

Dennis rolled his eyes, and suddenly a man with slicked-back hair and a tight long-sleeved shirt burst through the door “You guys, I just saw a pigeon outside eating- whoa what's going on?” Frank sighed, “Alright gang, meeting in my office.” The group slowly walked into the back room and y/n was left alone in the bar.

“Alright, let’s take a vote on whether or not we should hire this girl to be our new waitress” Mac leaned against the wall and folded his arms, “Why would we need a new waitress? Dee barely does anything already” Dee made a squeaky noise “You know what, YOU barely do anything you're supposed to be checking IDs and you have to be reminded to like every day.”

The two started to bicker before Frank interrupted “Whoa, Whoa, we still need to vote. Who wants to hire her?” Dee, Frank, and Charlie raised their hands and Mac grumbled. Dennis rolled his eyes, “It’d be a waste of money but Frank would be the one paying her, so I could care less”

Dee celebrated and left the office to talk to y/n, while Frank got settled in his chair. “Why do you even care Charlie? You don’t serve drinks and this girl is a stranger.” Mac huffed, “Well she let me crash on her couch and didn’t take me up on my sex offer so I owe her, and she’s really nice.” he said before staring off into space, while Mac turned to Frank.

“What about you? Why would you want to waste money on her?” Frank shrugged “The Gang could use a new face to pretty the place up, besides-” He leaned in closer to Mac, “Charlie could use a new lady who might actually be into him, and if I ever need the apartment I can send him next door so it’s a bonus.” he whispered in his raspy voice.

Mac sighed and he and Dennis left to the bar with Charlie following behind. Y/n was deep in conversation with Dee about how Dee wanted to act when Charlie sat beside her and Dennis put on a fake smile, “Well y/n, welcome to the gang. Or at least the staff, maybe I could take you to dinner at this hot new place in town.” She smiled, apparently unaffected. 

“I’m flattered, but I’m just not attracted to you” He looked confused and Dee held in her laughter while she turned to Charlie with a smile still stuck on her face “But maybe we could all go out for some cheap pizza to celebrate?”


	3. The Bet

Y/N started to get up and almost fell over, “oh boy, on second thought I think I should sober up right now, guess morning drinking is for pros and not lightweights.” The Gang hummed in agreement. Charlie reached out and clumsily helped her to her feet.

“Whoa y/n, you need to work on your balance” She started to laugh and grabbed her bag, “Thanks Charlie, you're sweet.” she stood and straightened herself up, leaning over to give him a quick peck on the cheek 

“I’ll see you all at seven, oh! and at lunch” she pulled out a pad of sticky notes and wrote her number and email on it, handing it over to Dee. “Here’s my contact info, message me the information and I’ll be back for lunch. Bye!” she waved goodbye before leaving the bar, walking home. 

Dennis shook his head, confused and flustered “Charlie? Sweet? Me not attractive? What kind of woman did you find? Is this another prank Frank?” Frank stepped out of the office “Calm down Dennis, she’s no prank. She’s just into Charlie” 

Dee scoffed, “Well it does seem like a prank if she’s into Charlie, I mean he’s like a raccoon, he eats trash and is practically rabid” Charlie rolled his eyes “She’s not that into me, I asked her if she wanted to bang and she said no. Besides, I am sexy as hell so why is it weird if I'm the one she's into?”

Mac side-eyed him and nodded “Uh-huh, well something is weird with her. Dennis has a foolproof system and it didn’t work, so something is wrong with her” Dennis shook his head, “No, I’m sure this is just a fluke, I will have her. And she will never be satisfied again”

Charlie made a grunting noise and stretched his legs, “Well I’m gonna go bash some rats in the back room, I swear I've heard something in there, good luck with your sex scheme.” He grabbed his rat stick and went into the back. Frank glared at Dennis, “Dennis, you can’t sleep with her, Charlie needs to get over the waitress for good and this is the only way” Dennis shrugged 

“Tough titties bitch, by the end of the month I’ll have her making me dinner and waiting up for me just for the chance I’ll take her to bed again.” Dee cringed, “That would never work on that woman, I’ll put money on it.” Mac perked up “I’ll take you up on that action, Charlie wouldn’t leave the waitress anyways, he’s always been obsessed with her, and if y/n can’t have Charlie…”

Dennis smirked, “She’ll fall right into my trap, and be so lonely she’ll sleep with me” Mac looked confused for a second “So you are trapping women?” Dennis squinted, “What? No, it’s just a figure of- you know what I don’t have time to keep explaining this to you just stay out of my way and let me work”

Mac shrugged and the group faded off doing whatever they had got into their heads when y/n walked back into the bar at noon, changed into old worn jeans and a sweatshirt with her purse. Dennis smiled at her and she smiled back, “Hey, where is everyone?” He shrugged, “I don’t know, Dee said something about needing Charlie to write a song for her to make someone jealous, they’re in the office.”

He winked at her as she began to walk towards the office, opening the door to see Charlie yelling about how he couldn’t write a love song for Dee because he didn’t love her and Dee making frustrated sounds, y/n barely held back her laughter and smiled at the pair “So are you guys ready to go out to lunch?”

Dee dropped a random pipe she was holding and seemingly lost all interest in what she had been fighting about with Charlie, and Charlie was simply happy to drop the plan for pizza. He walked beside y/n as Frank, Mac, and Dee were engaged in their own conversation ahead of the group while I walked between Dennis and Charlie.

Dennis was spinning a story about how he had a dog who was missing but she ignored that, Dee had warned her beforehand when they hired her about his pick up lines and she just assumed he was the kind of guy who likes the thrill of the chase, which meant her telling him he wasn’t attractive just meant that she was playing hard to get and not actually meaning what she said.

She was really listening to Charlie talk about some of his dreams and cats, watching how quickly his face would change with each detail of his stories. Dennis’s story kind of sounded like something you would read on Reddit someone only posted for upvotes and would never happen in real life. Also, why would he have his dog tied up outside the bar if he was holding the leash and collar?

The gang pooled into a random pizza place, ordering. Y/N sat with her head resting on one hand and a slice in the other, listening to Dee argue with Frank and Mac holding himself back from eating too much. Dennis and Charlie talking to some homeless guy outside the restaurant.

Mac glanced at Dee and whispered something about how Dennis was winning when she suddenly gushed to y/n about how Dennis got married to a cat, which made no sense to her when Mac got in on it talking about how Charlie drank paint. Frank then talked about the greatest prank he had pulled on Dennis, which shut Dee and Mac up.

She nodded and made her way to the bathroom when Frank confused himself in his own story and was untangling it with Mac and Dee. Dennis stood by her while she was waiting in line, asking if they could start over again and just be friendly, which she happily agreed to before he left to go eat with the others and she slipped into the bathroom.

Charlie was arguing with Cricket about how he didn’t have any information about Dee’s dating life, which he honestly tried to know the least amount about. Mac and Dee were arguing about the rules of the bet, and that telling y/n honest facts about Charlie and Dennis was fine while Dennis was telling them to stay out of his way.

Meanwhile, Frank thought about things he could do to set up Charlie with their new waitress and get rid of Dennis, and amping Dee up to fight with Mac seemed like the best option for now, even if it did little at the moment it would surely explode at the perfect moment and suddenly Charlie would have a cool lady and leave The Waitress behind.


	4. The Plan

Frank pulled Dee aside and whispered “Deeandra, I need you to go convince y/n to ask Charlie out tomorrow night, I’ll handle Charlie just don’t let Dennis get near her” Dee sighed “Why can’t Charlie ask her out, I will not let Mac win with his stupid face and weak insults” Frank grunted, “Deeandra, Charlie’s never going to make the first move while he’s hung up on The Waitress he needs a little push, go do your girl thing and convince her to seduce him. I’m gonna tell Charlie we’re hosting a date night for couples so he’ll ask y/n as friends so it won’t be a big deal, and her asking him first will be cool”

Dee shook her head. “Ugh fine, you work on Charlie I’m not losing any money to Mac.” Dee walked off into the women's bathroom and Frank looked over at Dennis looking smug sitting with Mac. Frank waved his hands in dismissal and walked over to Charlie who had come inside and eating, “Charlie, you need a hot date for tomorrow night” Charlie looked up from his slice, confused “Why? Is something happening tomorrow night?” Frank glanced around “Uh yeah, I’ve got to impress some rich broads and I can’t have you around if your single it’s like a couples party”

Charlie scrunched his face up “What? Well what about Dee, Dennis and Mac? “ Frank glanced at Mac and Dennis and suddenly had an idea “Mac and Dennis are going together as a couple, and Dee already has a date with a dude she’s been banging” Charlie sighed and rubbed his hands on his pants. “Shit, well maybe I can ask y/n, we’re friends so it should be cool, now what exactly is the plan?” Frank grinned “This group of rich broads run a couple date night group and they’re looking for a bar to hit every Saturday night to schmooze with other wealthy couples and politicians, so we’re all gonna act like we’re in happy relationships so they make our bar their new spot and we make a ton of cash”

Charlie nodded, “Well I like that, ok I’ll ask y/n” Frank grinned at his response and went outside to invite an actual couple’s group to the bar so Charlie wouldn’t figure it out, but he made the mistake of accidentally inviting a swingers couple group instead.Dee opened the bathroom door to see y/n washing her hands “Oh, hey Dee” Dee smiled, she was half expecting her to tell her to get out and call her a bird, but y/n was way too nice to do that after having only known her for a day.

“Heyyy y/n, so like the bar is hosting a couple’s night tomorrow to get some business and you're gonna need to have a date to play your partner so we fit in, everyone has a date, I have a hot new dude, and Mac and Dennis are together..” y/n was confused “I thought Dennis was straight, he tried to hit on me the moment we met” Dee glanced away from her “Well, you know he’s just being playful, he’s a flirt but he and Mac are totally together. Y/N nodded “Wow I would never have guessed, well except for Mac”

Dee smiled, victory was hers. “Yeah the only one without a date is Charlie so you can ask him, I know you guys are friends so it shouldn’t be weird, I mean you just have to act a little lovey dovey till they leave and bam, we’ve got some serious business and the bar becomes a hot dating spot. Y/N smiled, “Yeah that sounds like fun, I’ll go ask him and see if he’s into it, alright bye Dee!” And with that, she had left the bathroom. Dee fixed her hair in the mirror and celebrated her small win.

Y/N gently closed the door behind her and walked towards Charlie, “Hey Charlie, I was just wondering if you wanted to be my date for tomorrow night” Charlie smiled, “Hell yeah, Ooh do you want to do accents or something?” the question and made y/n laugh and start to nod before Frank sat down again and shook his head “Nothing weird Charlie we’ve got to impress.. Uh the group and make sure they keep coming back and we have a relationship with.. The group. Charlie looked confused but shrugged “Ok”

Y/n smiled at him and everyone finished lunch and made their way back to the bar to clean up and get ready for a busy night. Y/N had told her friends she worked there now and they had told their friends who told their friends, so she had brought a large crowd with her when she changed jobs. Dennis watched her from behind the bar like a predator, and was impressed with her social skills. She didn’t seem like the type of person to have so many friends on her own, and watching her it seemed like her small group of friends were the social butterflies and brought the crowd.

She seemed to know how to network and have friends in high places, which made him want her even more. Dee was struggling to keep up with y/n, it was clear she had been doing this for a while and she was more skilled in waitressing, but it was so nice to have the help it felt like she barely had to do anything. Frank was chatting up a lady who looked sloppy enough to go home with him and keeping an eye on Dennis, who was flirting way more with y/n than before, but she seemed to be more accepting of it and even smiling now and then. 

Charlie had been cleaning the glasses, not with bleach which Dennis insisted on, and joking around with y/n when she came to the bar to pick up drinks. Mac was having the time of his life checking I.D. 's, there were a lot of hunky dudes walking in and chatting with him and he felt super tough and hot. Everyone slowly started to clear out and Charlie cleaned up while Frank and Dennis counted the money, and Dennis grabbed a cold beer, handing it to y/n. “To y/n! Without her hot body we wouldn’t have had such a successful night, welcome to the gang!” 

Everyone cheered and grabbed a beer, making y/n blush. “Thanks guys, now let's keep the success going for tomorrow night!” Mac and Dennis looked a little confused but shrugged it off, and the gang slowly parted ways for the night. Frank and Charlie offered y/n a ride home which she gladly accepted and they spent the ride home talking about boiling denim.

**Notes for the Chapter:**

> Thanks so much to lovely people commenting and making my day! Hope you all enjoyed the latest chapter


	5. The Waitress vs. Y/N

Frank parked and Charlie walked y/n to her door, “Hey thanks so much for getting me this job it means a lot,” she said before going in for a hug, wrapping her arms around his middle and pulling him hin, tucking her head in his neck. Charlie stiffened like he wasn’t used to affection but slowly accepted it and gently hugged back awkwardly, y/n giggled and wiped a few tears from her eyes “Hey, it’s not a big deal or anything like you helped me first and let me stay with you, don’t worry about it” She grinned up at him and let him go from her embrace, playfully shoving him.

“This isn’t some kind of thing where you're doing this so i’ll bang you right?” she teased, causing him to flush red and rub the back of his neck “Hah yeah sorry about that, but we’re friends now right?” She smiled at him the way that made him regret ever saying the word ‘friends’ in his life ,“Of course, thanks for being my date I swear next time we pull a dating scheme i’ll bring my own date so you can go with someone you like” He laughed awkwardly and nodded, “Yeah ok.. I’ll see you later” He waved and they both separated into their own apartments, y/n crashing onto her bed and biting her lip.

Why did she always fall for guys who were never into her that way? Charlie sighed and roughed up his hair, going to sit on the couch. It’s not like he was dating The Waitress right? But he was a loyal guy, and sure y/n was pretty and nice but he hadn’t been obsessed over HER for years. Frank walked into the apartment and glanced at Charlie “What’s wrong? Did something happen?” Charlie sighed, “It’s just ya know she hugged me but does that mean she just wants to be friends?”

“And I don’t even know if I want to just friends or like date her cause like I love The Waitress but she doesn’t love me and she has a restraining order on me so it’s like does she ever want to date me or is it just me?” Frank shut the door behind him “Ok first of all you need to slow down Charlie, and second of all she’s a nice lady so wouldn’t it be a good thing if she liked you?” Charlie rolled over and screamed into his pillow. Frank walked over and sat down on the couch “How about you call The Waitress and see if she would ever want to date you, and move on from there?”

Charlie slowly let go of his pillow and nodded, “Yeah ok, I’ll call her and if she wants to go out with me as my date night date tomorrow and if she says yes I won’t go out with y/n anymore” Frank sighed and let Charlie make his own mistakes as he started to call The Waitress. She picked up after a while “Hello?” “Hey Waitress, I was just calling to see if you-” “Charlie? How did you get this number?” “What? Oh Dennis gave it to me, anyways I was just seeing if you wanted to help out in a date night scheme tomorrow night?”

The Waitress sighed “Will Dennis be there?” Charlie looked puzzled “Uh yeah but he’s going with-” “Great, I’ll go with you just don’t touch me” and with that she hung up. Charlie looked down at his phone “Well she said yes and the only thing I have to do is not touch her, but she didn’t say I couldn’t talk to her! So that’s good news, I’ll go tell y/n I have another date, thanks Frank!” Frank sighed and shook his head.

There was a knock at y/n’s door and she got up to go answer the door, checking the peep hole and smiling when she opened the door “Charli? Didn’t we just say goodbye?” she laughed and Charlie grinned, “Yeah but about tomorrow night, I have a date with the love of my life so im sorry but i'm gonna go with her, anyways thanks goodnight!” And he was gone. Y/n sighed and shut the door, hurt. Suddenly her phone rang, it was an unknown number. She answered and went to sit down.

“Hello?” she questioned, “Y/n! Hey It’s Dennis, so I just wanted to tell you that I’m not gay,” She heard what sounded like Dee grumbling in the background before Dennis carried on “Anyways I was wondering if you wanted to be my date for tomorrow night” Y/n sighed, “Sure, I’ll see you tomorrow.” She hung up and turned on her radio, The Killers ‘When You Were Young’ immediately began playing and she began picking out her outfit for tomorrow night. She had hoped she would have a fun date with Charlie, but it seemed like they were just friends.

Frank grumbled and tossed and turned in bed, and Charlie huffed “What dude? I need to be well rested and stuff for my date with The Waitress.” Frank turned to Charlie “She's only going to bother Dennis, you know y/n actually likes you and want’s to go out with you and you pick The Waitress instead? What’s so special about her? She’s not even nice to you.” Charlie sighed “I just do ok? I don’t know why. Besides, y/n will probably be fine.”

Frank grunted and sighed, “Well if you want to lose her to Dennis, go ahead Charlie but your gonna miss out on a great broad” Charlie huffed, “You know what dude I’ve heard enough, I know what I want and I don’t want to be lectured, I’m going in the crevice” “Charlie don’t go in the crevice” “I’m going!” Frank sighed and turned “Fine, I hope that makes you happy and you don’t miss out” Charlie just grunted and turned away.


	6. The Gang Swings

Charlie grumbled as he got out of bed, Frank had said something about getting up early to get decorations for the bar and had left early without him. Charlie felt a little bit guilty leaving y/n behind for The Waitress, but she was the love of his life! He wasn’t going to go down without a fight. He was rummaging through some of his nicer clothes and picked out a blue button-down and gray suit jacket, and he’d just wear some casual jeans.

He got dressed in casual clothes to go and steal some flowers for The Waitress. As he was leaving he spotted y/n walking towards him wearing a white button-down shirt tucked into her godet skirt. She smiled at him and held out two cups of coffee, which made him feel warm and bubbly inside, like he had suddenly caught the flu, or was trapped playing quarantine with the gang again.

He smiled back at her and she stood beside him, “Good morning, you look happy today. Want some coffee?” He nodded and took a cup, brushing his hands against hers. “Thanks, yeah you look good too, did you find a date for tonight?” He asked before taking a swig from his cup, and she nodded “Yeah Dennis called last night and asked me, apparently Dee thought he was dating Mac.” Charlie almost choked on his drink.

He hadn’t expected Dennis to actually win y/n over, it felt almost wrong to think of them together in any way. It made his stomach churn. He cleared his throat, “Oh? That’s weird I mean I could see Mac and Dennis as a couple and they do live together so ya know… But that’s totally great you found a date and stuff,” He stared into his cup of coffee, “So yeah I’d be careful with him though, he doesn’t date girls like long term.”

She eyed him for a second and turned her head away to drink, “Yeah, well we’re just playing a cute couple, not actually dating. So I’m not worried about him breaking my heart.” She laughed. He looked relieved for half a second before he continued talking “Anyways yeah, I got to go... Now.” He left quickly and y/n sighed. She was confused, all these mixed signals left her confused.

The day breezed by and Charlie had changed into his nice clothes and wrapped up the stollen roses and was waiting at the ba,r now decorated in cheap shiny Valentine hearts, for The Waitress. The couples in the bar didn’t seem like rich wealthy people they seemed pretty weird but he brushed it off, he was focused on his date with The Waitress. She walked in wearing a sundress and rolled her eyes at him, but went to go sit with him anyway. “So where is Dennis? Shouldn’t he here be tending bar?”

He looked around just as Dennis opened the door for y/n, wearing her same outfit, she had just swapped her sneakers for heels and put her hair up. She waved at him and he pointed over at Dennis for The Waitress, and she quickly left him to go talk to Dennis. Y/N looked surprised but she turned and walked around her over to Charlie “So that’s your date?” 

Charlie cleared his throat “Um yeah, she ya know likes to talk Dennis and there’s nothing weird about it at all so let’s not talk about it” Y/N shrugged “I get it, I’ll back off.” Charlie smiled at her and Frank walked over, guiding a couple that seemed to be the leaders of the group date night thing. “And This is y/n and Charlie, one of Paddy’s Pub's favorite couples. They’ve been together for years.”

Charlie glared at Frank before smiling at the couple, who introduced themselves as Andy and Carol Hayes. “Yes, we actually met here and got married here. We are a very happy couple.” Y/N chimed in her own to have some fun. Charlie nodded “Yes we have eight cats instead of children.” Y/N held back her laughter. Dennis walked over, trying to shake The Waitress when Frank grinned.

“And this is Dennis and his wife, Dennis is our bartender” Dennis looked at The Waitress grinned slyly and the couple turned their attention towards them. “No! Frank must be mistaken, I have a boyfriend I would never date a woman.” “Honey, what are you talking about?” The waitress teased and tried to wrap her hands around his waist. “Ooh spicy, our group is welcoming to all kinds of swinging couples”

Dennis turned to the woman, “What?” Carol looked confused “Our group is a swingers group, we get together once a week and dance and go home with each other.” Dee snickered and elbowed Mac, queuing him to go flirt with Dennis. Mac smirked and pulled him away from the rest of the group, and bringing him into the crowd so he could flirt with him. The Waitress sighed and walked over to Charlie.

“Who's this girl? Did you hire a prostitute to make me jealous, Charlie?” Y/N glanced at Charlie and The Waitress, “Umm what? Look I don’t want any trouble ma’am I’m just having a conversation with my husband with whom I raised eight cats with” The Waitress rolled her eyes “Ok seriously what’s going on?” Charlie placed a hand on y/n’s shoulder “No dude this is The Waitress, the love of my life!”

Y/N perked up “Oh! Oh my god hi, I’m y/n, I’m sorry I thought you were one of the swingers I didn’t know you were Charlie’s girlfriend” The Waitress relaxed and shrugged “Oh I’m not his girlfriend, no never not in a million years. I’m going to get drunk and seduce Dennis.” and with that, she was gone. Y/N slunk back down on her chair “Oh I’m so sorry Charlie, um are you good?” 

Charlie cleared his throat “Um yeah of course I am, why wouldn’t I be?” y/n eyed him, confused “Um, you just got rejected..?” Charlie scrunched up his face “What? No dude this happens all the time- Ugh ok fine” y/n reached out and patted his shoulder “It’s ok, we all strike out every once and a while, the night is still young! Let’s have some fun, my loving husband and father of my eight cats, how about a dance?”

Charlie nodded and sighed, “Yeah let's join the swingers in a non-sexual way.” y/n laughed and stood up, offering Charlie her hand, “Shall we, darling husband?” He reached out and took her hand, “Of course, wife I married for the money” she laughed as she pulled him in, taking the lead. “Ooh, I’m the rich one? Cool.” “Of course! I’m the hot arm candy, a trophy husband who spends his day raising his cat babies”

Y/N twirled Charlie around and interlaced her fingers with his, moving closer together. “And of course I’m the businesswoman, keeping my man and cats in the finest clothing.” He nodded, smiling down at her as they swayed, most of the group too busy with their own petty drama to notice the two slow dancing to a song not meant to be slow danced to. Y/N blushed under his gaze but she just grinned with him.

She slowly moved one hand up his arm to rest her hand on the nape of his neck, gently pulling him down for a gentle kiss, his lips chapped but welcoming to her much softer lips, she almost didn’t want to let him go. He was warm and comforting in a way, he tasted like beer and cheese, and he suddenly smelled so good it confused her. He let go of her hand and snuck them around her waist, one gripping her waist and the other pulling her in by the small of her back.

His beard tickled and she pulled away giggling. “Sorry, I’m just a bit ticklish, you're not a bad kisser or anything.” He looked away, “Hah, yeah it’s fine it didn’t mean anything we just got caught up in a moment ya know?” She laughed before pulling him in for another kiss, this time cupping his cheeks and kissing him harder “Oops” She muttered after pulling away for air, moving her hands down to rest on his neck.

Their moment quickly ended after Frank and Dee started yelling about god knows what, and y/n looked to Charlie "Do you want to sneak out of here with everyone else?" He nodded and they held hands as the hid in the crowd, beginning to walk home, their arms swinging as they strolled the streets. He turned towards her and she could see his breath in the chilly night air. "So does this mean we're like seeing each other now?"

She stood still and faced him "Do you want to see me? like exclusively?" He shrugged, "I don't know yet, I've been in love with The Waitress for so long it's hard to imagine dating anyone else" y/n shrugged "That's ok, I get it" She leaned against his shoulder "We can just figure it out with time, don't worry about it right now." He smiled and wrapped an arm around her waist, pulling her in closer as they walked home together. 

He stopped at her door and she looked up at him "Thank's for walking me home, even if we are neighbors it was sweet of you" He turned his head away "Oh ya know, it was nothing really I was just walking home a friend girl or something" y/n pulled him in for a goodbye/thank you kiss. It started to get more heated and they pushed up against her door, he started to lift her up when she stopped him. 

"Umm, I get that you don't want to be dating yet, but I have rules and boundaries too, I don't sleep with friend boys" She slowly let him go, "Though I'm happy to kiss you anytime" She left him in the hallway, locking her door behind her and Charlie shoved his hands into his jean pockets and went into his own apartment, waiting for Frank to get home and tell him what happened at the bar.

Apparently, Dennis was stuck between The Waitress and Mac, but eventually left with Mac and The Waitress left the bar with some Swingers. Frank almost did the same but Dee got into a fight with one of the couples, as she thought she was exclusively dating a hot successful man, who turned out to already be married. So she spent the night cleaning up after everyone's brawl. Frank came home in a bit of a grumpy mood.

It seemed as no one had noticed y/n and Charlie all night so he was relieved and disappointed at the same time. He told Frank about The Waitress rejecting him and dancing with y/n but left out the juicy details. 

Y/N got a text from Dennis while she was brushing her teeth, inviting her out to dinner because their date was interrupted before they could spend some time together. She agreed to go out with him, as friends of course. She didn't want to mess up things with Charlie but didn't want things to be awkward at work. 

Dennis was at home, ignoring Mac for putting him in that situation. He had seen y/n and Charlie dancing and didn't want things to get out of control and have her be suddenly taken away from his grasp. He planned to get her tipsy and take her home, so at least Charlie would think that they slept together and leave y/n brokenhearted. He laughed maniacally and Mac walked into his bedroom, "What are you doing dude, you're being creepy" 

Dennis glared at him, "Nothing don't worry about it, also stop telling people we're a couple!" Mac sighed "I didn't start that rumor I swear dude" he raised his hands, leaving the room. Dennis looked at himself in the mirror. If Mac didn't start that rumor, that would mean... "Charlie... That bastard" he cursed.


	7. Chapter 7

**Summary for the Chapter:**

> This took me an embarrassingly long time to write, but I hope y'all enjoy it!

Y/N woke up the next day with a tinge of regret, she wished she had told Charlie, "No, hey I want to date you so if you don't want to date me, say so!" It was incredibly frustrating to want to date someone who isn't ready to date you.

She tossed and turned in her bed, procrastinating getting up. Sometimes she wished she was in a movie and everything could be perfect and the guy she liked was head over heels in love with her and she was never the second choice.

She sighed and rolled out of bed, this was what happens when let herself get pushed over. It wasn't Charlie's fault, he was honest, and she wasn't. She didn't want to lose Charlie, but she felt she should keep her options open. 

She put on her favorite music and got dressed in a white button-down and a high waisted, knee-length denim skirt. If she was going out on a date with Dennis, she was going to make the best of it. She put on a pair of sneakers and a pair of heels in her bag for later that night.

Y/N went to make herself breakfast and sang along to her favorite song. Sure, people were yelling out in the hall and the building was mostly cats and rats, but this was HER place. She didn't need to worry about a guy she may or may not be dating.

Charlie woke up in a bad mood, he didn't know why, other than the fact he shared a pullout couch with another man, who was grumpy he didn't get to participate in an orgy. He checked his phone to see a message from Dennis, with just an evil-looking man emoji. 

And that didn't help him either. He got up, stretching his back and hearing a popping sound, and a level of pain that sent him face-first into the floor. Frank struggled to get up, eventually just falling onto the floor himself. 

"Charlie! What happened?" He called out, crawling on his hands and knees over to him. Charlie screamed out in frustration. "Ok, Frank I need you to get me up and pop my back" Frank nodded, "Ok, there's just one problem. I can't get up"

Charlie let out another scream. 

Y/N was locking her door, ready to head out and cross off a few errands from her list and be done by the time she had to get to dinner. With a laundry basket under her arm, she passed by Charlie and Frank's apartment when she heard some high pitched, almost feminine screams coming from there.

She paused and inched closer to their door, hesitantly knocking "Um, everything ok in there?" Charlie could jump for joy if he could stand. "Y/N oh my god, Frank and I are stuck on the floor, can you break in the door?" "Oh my god, are you sure you don't want me to call an ambulance?"

"No!" he shouted, startling y/n. "I mean, I don't have insurance, I'll be fine if you can just pop my back." Y/N sized up the door and sighed "Ok, here we go" She said dropping her laundry basket, running towards the door, hoping to cave it in with her shoulder.

A thud hit the door, followed by sounds of pain. "Uh, guys? Yeah, this isn't going to work" Charlie groaned, thinking. "OH! Call Mac, he'd kill to kick open a door." Y/N leaned against the door, not wanting to get up while she was hurt.

"Ok, what's his number?"

It didn't take Mac long to show up, with an old school camera and stuff to film it for some stunt videos? Y/N didn't quite get it but she stayed out of his way and watched him kick in the door. It took a long time for him to do it, but he did.

He walked over to Charlie and Frank and started to crack their backs as if it was just a normal thing that happened every day. They both looked pretty messy, but Charlie looked so cute, well as cute as a 40-year-old who had just been stuck on the floor could.

She rubbed her shoulder, sore. "Well, that was fun... But I've got to get going" Charlie nodded, "Yeah thanks dude" Frank elbowed him and he grumbled "Uh, do you want to like hang out?" Y/N eyed him and nodded, smiling a bit "Yeah sure!"

He got up and started to leave before Y/N stopped him "Uh, do you want to change before we go out?" She said, eyeing his... Long underwear? He looked down and laughed "Oh shit, yeah" Y/N smiled and walked out of their apartment.

"I'll meet you outside!" She called out as she grabbed her laundry and left, heading downstairs to the main entrance and browsing her phone, checking with Dennis where they were going to dinner when Charlie burst through the door and Y/N clicked her phone off.

He stopped and leaned against the door, trying to appear sexy "Hey..." This made Y/N laugh and she reached out to grab his arm. "Come along, let's get this done no matter how hot you are" "Oh yeah that worked?" "I'm practically burning up"

She held his hand as they walked, her other arm carrying her things, walking into a laundry mat. The place was fairly empty and Charlie just sat on the counter watching Y/N do laundry "You know I've lived in this neighborhood forever, never been in here"

"Really? How do you do your laundry then?" He shrugged "I usually take it to my moms, she's got a washer and dryer" Y/N smiled "Oh how nice, you're close with your mom?" He nodded, sorting through her clothes mindlessly "Yeah, I mean I love her and stuff even if she shares too much"

Y/N smiled to herself, "Seems like a mom thing, to say stuff that's like TMI" Charlie came across her underwear as they reached the bottom of her laundry basket, which she snatched from his hands and threw it in the washing machine.

"Uh, thanks for your help, it means a lot" He smiled at her and stuffed his hands in his pockets, looking down "Ah It's nothing, I mean without you I'd still be stuck on the floor." Y/N laughed and leaned against him, tucking her head into his shoulder.

Charlie flushed red and cleared his throat, "So uh, did you want to get dinner or something?" Y/N pulled away and sighed, "Um, I'm already going out tonight... With Dennis" Charlie raised his eyebrows "What? But I thought me and you..."

Y/N sighed and looked away from him. "Charlie, we're not like exclusive, I know you still love The Waitress even though she's mean to you" Charlie scoffed, "Yeah but like she's the love of my life, and you..." Y/N went silent.

"I think you should go Charlie."


	8. Not Fair

Charlie huffed and hopped down from the counter, "Fine." He left and Y/N turned to sigh, a tear slipping down her cheek that she wiped away quickly before anyone could see her cry. Sometimes she hated how she couldn't control her emotions. She was still mad at him, he had no right to react like that.

If he wanted to be exclusive, he should have said so when he had a chance. And expecting her to just wait around for him to give up on The Waitress was selfish. She groaned and looked at herself in the little cracked mirror above the counter, fixing her hair.

It's not as if she was trying to go out and get married, it was ONE dinner with a man who was terrible at flirting. And according to everyone else, he wasn't looking for a wife either. Charlie wasn't in a rush to settle down even in the smallest way, like having a girlfriend. 

She watched the clothes spin till they were done, zoned out till she heard the buzzer blare in the empty laundry mat. She hopped off the counter and sorted her clothes, spotting a sparkly red dress in her wash she had forgotten she'd put in. She decided then and there, she was going all out on this date.

Charlie grumpily walked back home, not fully understanding why. She was right, he didn't want to just date her yet, and if The Waitress asked him out to dinner he would drop everything and do it, so why was he upset? Maybe because it was Dennis, who had sworn to make her his just days ago.

But thinking of other people doing the same thing with Y/N didn't make things better, or worse. It was all bad. Charlie didn't know who to turn to, as Dennis was the one going out with Y/N, and Dee was terrible at dating. Frank was weird about Y/N and The Waitress, and would probably tell him to just leave The Waitress behind.

He decided to turn to Mac, as it was pretty much his last option. Even if it meant he would run into Dennis. Soon enough, he found himself at their door, knocking. Mac opened the door and Charlie pushed past him, checking to make sure Dennis wasn't there "Hey dude, wheres Dennis?" Mac looked confused, "Uh he said he went out to buy condoms, why?"

Charlie groaned, "Ah dude I don't want to hear what he does, I'm already stressed about their date I don't want to know any details." Mac shrugged, "You asked dude, besides you want to know SOME of the details, right?" He asked as he shut the door and went to crash onto the couch. Charlie sighed and shook his head, "Well maybe I want to know some details, but not the gross one's dude"

Mac pointed to the fridge "Get us some beers and I'll answer your questions" Charlie threw up his hands "Yeah yeah," He grabbed two bottles and opened them before going to sit with him "Ok, so tell me what's going on" Mac grabbed the bottle and leaned back, "He's doing the same thing he always does, wine and dine fake out and bring her back here and you know the rest" 

Charlie fiddled with his drink, "Ah dude I just, no she wouldn't sleep with him on the first date. She's not like that..." Mac shrugged and took a drink "How do you know that? You've only known her for a few days, and Dennis for forever. And he always gets the girl" Charlie grumbled "No dude he- ya know what, this isn't helping. I made Y/N mad and I don't know how to fix it"

Mac thought for a second, "Have you ever thought of choreographing a dance or writing a musical for her?" Charlie looked at him like he was crazy, "Of course! Dude that was the first thing I thought about but it would take forever for Artemis to translate it and shit" Mac nodded, "Well maybe you should call her and talk it out with her. Or... We could go and spy on them? Make sure he's not trying to trap her" Charlie took a swig from his drink "Well, to Dennis it's always a trap I mean that's his whole thing" 

Y/N walked home alone, putting her clothes away quickly and getting dressed up, she was meeting Dennis at the bar and didn't want to look bad at this supposedly really nice restaurant. She got a ride from one of her friends and had been waiting for about half an hour when everyone came crashing in. 

Y/N stood up quickly, going to check up on the pile of men on the floor. It looked as if Dennis, Mac and Charlie had rammed into the door at the same time. Y/N crossed her arms, "What's going on here?" Charlie scrambled to get up, Mac seemed happy to be on top of Dennis. "Um, ya see we, uh, we wanted drinks" She looked at him confused "And you wanted a drink so bad you, were fighting to get into the bar?" 

Charlie leaned against the wall "Of course yeah we do it all the time, and hey! Look at you, so pretty by the way... Do you want me to take you out instead while Dennis is doing whatever on the floor?" He held out his hand for her to take, while Dennis was pushing Mac off of him "Get off of me you idiot," He scrambled up, dropping a box of condoms all over on the floor. "Um, wow ok. Y'know I think I'll just go home, and let you sort whatever the hell your doing" 

Dennis stood up quickly and reached out to grab her arm "No it's fine we're still going out to eat, can't let these idiots get in the way of our fun night, right? Yeah let's go" He took her arm and glared at Mac and Charlie. Charlie grumbled and helped Mac to his feet before following Y/N and Dennis outside "Yeah, Let's all go out to dinner, as a group!" Dennis started to argue with him but Y/N pressed a hand to his chest, stopping him in his tracks.

"Look, Charlie, if you didn't want me to go out with anyone else, why didn't you say so last night?" He started to stutter and look around "Uh well... I don't know man. I just, I don't want to like settle down yet but like I don't want you to go out with other people." Y/N glared at him, "Charlie, that's not fair for you to ask that from me."


	9. Chapter 9

Y/n stared down at him and shook her head "Just go, Charlie" He looked like a heartbroken puppy and Mac refused to make eye contact with her. She rolled her eyes and pushed him away "Go home Charlie, and stop making that face I can't- stop it" Charlie looked away and Mac dragged him away.

Dennis put his arm around her waist and they walked to his car. "Wow, you really had Charlie under your full control and you've only known him for a few days... That's insanely attractive, we may have more than a one-night thing with that kind of attitude. Usually, I prefer to be the one in control"

Y/N looked at him like he had grown two heads and slowly looked away from him, watching the buildings as they passed by. She was surprised when he actually took her to a restaurant that was open, Dee had warned her before that was one of the things he did, and to call him on it if he tried anything. 

He helped her out of the car and walked arm in arm with her, the place was very nice, though the waiter seemed kind of disappointed to see them which really confused Y/N. Throughout dinner, he was trying to get her to open up, which made her use the old reverse uno card to see what he was like under all of his make up.

Turns out it's pretty dark under there, but strangely interesting at the same time and she couldn't look away like a car crash. She had a nice time, even though he was desperately trying to break down her walls. She did agree to go back to his place in the end, to sleep on his couch. She didn't want to run into Charlie after everything. 

She held onto his shoulder so she could take her heels off, making Dennis stiff. She looked at him, confused but shrugged it off and waited for him to open the door. Behind the door was Mac quickly smothering what looked like to be a small fire while Charlie quickly leaned on a couch that looked to be singed.

Dennis glared at Mac and Charlie "What the hell are you doing you idiots! Did you set the fucking couch on fire?" Mac stuttered "Ah, no- no- no dude we didn't MEAN to set it on fire it just sort of happened" Dennis looked between the two so fast Y/N was surprised his head didn't fly off "How the FUCK did it catch on fire then?"

Charlie sputtered and leaned against the wall, "Well you see, we were TRYING to get the change out of the couch to pay for pizza but things got out of hand very quickly" Y/N walked over to the fridge and got herself a beer and let them work it out. Until Dennis started shouting about how he was trying to bang her. She slammed her bottle down and strode towards him.

She pulled him down to her height and slapped him "Stop being sleazy, now say sorry and go to bed, by yourself!" He nodded, "I'm sorry" He seemed to be.. getting off on it. He glared at Charlie and Mac before shutting locking a concerning amount of locks on his door.

Mac looked confused and eyed her, she just grumbled and sat down on the extra crispy couch to drink. She pointed at Charlie and snapped her fingers at him. "Sit, and stob being creepy weird and go back to fun weird, tell me what's up" He sat down and curled up in the corner of the couch and faced her. 

"I don't want you to date Dennis!" He blurted out, and Y/N sighed and took a sip of her drink "I don't WANT to date Dennis, I want to date you" He softened up and looked her in the eye. Mac looked in between them awkwardly and hurried away into his room. She reached out and held Charlie's hand.

"All I need to know, is would you be with anyone else while we are together?" He shook his head and Y/N pulled him in for a kiss, moving to sit on top of his lap. He rubbed his hands around her body rapidly, reminding her of her first boyfriend in high school. He seemed to get the hang of it though.

This clearly wasn't how she thought her night would be ending. She tugged on his hair and he moaned in her mouth and pulled away, looking confused. "Is everything ok?" He nodded, "Yeah uh, can you do that again?" She tugged on his hair from the roots and he moaned again. She smirked and he panted. 

"Does this count as boyfriend and girlfriend stuff?" She sat up and thought for a second before shaking her head "I don't think fooling around on your best friends burnt couch counts but it sure is fun" He laughed and pulled her back down to make out again.

They did that for a good half hour before Mac walked back out and groaned "Come on guys, go home" Y/N giggled and stood up, grabbing her shoes. "Wanna walk me home?" Charlie nodded and loaned her his green jacket as they walked home together. 

The crisp air and cozy company left Charlie with goosebumps and, as he liked to put it, moths in his stomach. She held his hand the whole way home, even as she unlocked her door. She pulled him inside and started just where they had left off when he stopped her. 

"Uh, I don't know if I'm ready to this yet" She stopped and sat down on her bed, watching him "Why?" He moved to sit across from her on the couch "Well, usually when I sleep with people it doesn't last long and they like leave. Or sometimes I do." Y/N nodded her head "I get it Charlie, we don't have to do anything you don't want to. But would you mind sleep sleeping with me?" 

He looked off for a while before eventually nodding "Yeah, ok." She grabbed some pajama bottoms with 'JUICY' bejeweled on the butt she had picked up from Walmart years ago because they were cheap and threw them to him before grabbing a big comfy shirt for herself. 

It wasn't long before they fell asleep together, Charlie tucked in her arms made her feel strong like a protector. Also, Charlie just ridiculously looked hot in those pants


	10. Chapter 10

Y/N woke up with Charlie, his legs sprawled out but her arms still wrapped around him, and he was dead asleep. Hopefully not actually dead. He probably wasn't used to sleeping in an actual bed instead of a pull-out couch. She smiled and let go of his waist and slipped out of her bed. She had a few texts from the Gang, Dee asking if she slept with Dennis and Mac asking if she banged Charlie. Those two were very forward, it seemed. Dennis asked if she wanted to go out again, with an eggplant emoji at the end of course. 

She left Charlie in bed while she went to take a shower and get ready for the day. Charlie sat up slowly, his back seemed to feel way better just from sleeping in her bed. He turned over to grab his phone, not realizing it wasn't his, from the bedside table, accidentally reading Dennis's text, well not reading just seeing the eggplant emoji, getting the point. 

Y/N walked in on him while she was trying to dry her hair with a towel. "What are you doing?" She looked at him confused and he threw her phone in a panic. "Uh.. nothing" "Charlie, you just chucked my phone at the wall. What's going on?" She walked over to where her phone had landed, thankfully she kept it in a case so it was fine. She read Dennis's text again and sat down on the bed by Charlie's feet.

"Charlie, I'm not going to go out with Dennis again" He looked confused, "He asked you on a date?" She looked confused, "Uh yeah, isn't that why you threw my phone?" "Well, I just saw the eggplant and thought you were hooking up with him" She looked at him, confusion on her face. "Oh, well I'm not." 

Charlie stood and stretched, "Sorry I didn't mean to be creepy, though some people might think it's romantic." He said, stretching out his arms as if to help his argument. She shook her head and scrunched up her face "It's not" He hung his head and dropped his arms back down to his sides. He looked up at her and slowly smiled, "But it could be right?" She laughed and shook her head again. 

"No, it's really not. But, I do have a question for you." She went in for a hug, which surprised him "Can you read?" He shook his head, "No I really can't, I mean I have a system of symbols that works for me so like I'm fine" She patted him on the back, "Good to know" She took his hand, "Well, you'll have to give me crash course while we go get breakfast"

Charlie left next door to get dressed and Y/N texted Dennis back a simple 'no' before getting ready to go out. She let Mac and Dee think what they wanted to, no matter what it wasn't something she would tell them, even her best friends knew she didn't talk about her relationships, to her their stories were always better anyways.

Charlie walked back inside, fully dressed and hair just as crazy as always. She looked away from the mirror she was using to fix her hair and smiled at him, going to take his hand in hers "Ready to go eat?" he nodded and they started to walk to a nearby diner. 

After breakfast, the two decided to just go to the movie theatre and make out in the back, Y/N's friend had given her some tickets she hadn't been able to use and they didn't care too much about the movie as it had been showing for a while and no one else was there. 

After a day of fooling around with each other, they found themselves back to work at the bar. Y/N was smiling at Charlie as she worked and Dennis glaring was at the two. Mac and Dee were mumbling to each other, unable to figure out if they had slept together yet and who had won the bet. 

Frank was in the back talking to, as he put it, "Some broad who had a thing for ol' Frankie" and then he started dancing and singing about how he still had the moves. Y/N didn't mind, she was having fun flirting with Charlie and teasing him. And Dennis was always weird. He seemed kind of broody though, and he snuck away to make a phone call. 

About half an hour, The Waitress walked through the doors and made a beeline for Dennis. Y/N frowned when Charlie started to get flustered around her. She put her tray up and went to splash some cold water on her face in the bathroom. Getting jealous would get her nowhere, and probably push Charlie away but she couldn't help it.

Dennis smirked when he saw Y/N retreat into the bathroom, he had won. Charlie was an idiot and would ignore Y/N all night, probably follow The Waitress home and He would get rid of one of the hurdles between him and his delicious prize. Even better...

When Y/N slipped back into the room and went to grab her tray, Dennis cleared his throat "Hey I have an idea, how about we all go for dinner after we close and have a double date?" The Waitress quickly agreed, as he knew she would and Charlie was quick to follow her lead, earning a glare from Y/N and she sighed and ducked her head, "Ok"

Dennis grinned and Y/N was tempted to call him a demon before she left the group to keep working. Time flies when you are dreading the end of your shift. As everyone slowly faded from the bar, she was tempted to cough and say she wasn't feeling well and disappear but Dennis grabbed her arm and walked with her. 

That seemed to break Charlie's spell, at least long enough for him to pull her back and save her from Dennis. He raised his arms in surrender and walked arm in arm with The Waitress instead, winking back at Charlie. He began to grind his teeth but stayed quiet, instead giving Dennis crazy eyes and walking with Y/N.

It was really late, so they ended up at a hotdog stand and after getting her food, Y/N separated from the group to go sit on a nearby bench and watch the three. Charlie and Dennis seemed to be in an intense staring contest and The Waitress really didn't care about Y/N's presence at all. Y/N grabbed her phone and earbuds, deciding to ditch the group.

She didn't care for any of them at the moment, Dennis and his manipulation, Charlie and his indecisiveness and The Waitress was just terrible company. She gave her hotdog to a man she had seen chatting with Dennis and Charlie, tucking her hands into her pockets and heading home.

It didn't take long before Dennis tried to scratch Charlie and they started to fight, The Waitress cheering Dennis on while she chugged a beer she got from the hotdog vendor. Charlie pushed Dennis away from him, "Just leave Y/N alone dude! She's not into you, and stop bringing The Waitress into this, she was once my true love but I'm trying to get over her!" 

The Waitress rolled her eyes and kept eating as she spoke to him "Charlie come on, your never gonna leave me alone I mean you couldn't even do that when I asked you to stay away, you'll forget Y/N in a week." Charlie crossed his arms and shook his head, slowly looking her in the eye "But I don't want to forget her in a week, and why would I? She actually kinda cares about me" The Waitress rolled her eyes "Look around Charlie, you've already forgotten her."

Charlie and Dennis both looked around, cursing once they noticed she was long gone. This really happened to them too much. They glared at each other before Charlie booked it, frustrated that he had let her go and he was going to go back to pining over a girl who didn't like him and fighting with Dennis. Dennis caught up with him and they ran into Cricket, who was busy eating a hot dog.

"Cricket you bitch, where did you get that?" Dennis shouted, startling the man. "Oh uh, the lady you guys were with gave it to me" Dennis grinned and pushed Charlie into Cricket, following the trail. It was obvious he was having the time of his life, he was hunting a woman. Charlie groaned and got up and started running after him.

Y/N was leaning against her building, listening to her music and feeling moody. She didn't like feeling jealous, and she just wanted to trust Charlie to stay loyal but it was still a new confusing relationship. She wiped away her tears and groaned. Dating was fucking complicated. She opened the front door and stomped inside, rushing to get to her apartment when she ran into Frank. "Hey! Have you seen Charlie? He was supposed to sharpen my teeth"

Y/N stopped and stared at him "What?" Frank shrugged and opened the door to his place "Wanna hang out and wait for him?" Y/N shrugged and they went inside. Frank was actually pretty fun to hang out with, and they ended up drinking together and watching Police Academy. Dennis and Charlie crashed into each other as they got to the building. 

Dennis smirked down at Charlie and grabbed the door handle, trying to open it but it didn't budge. Charlie grinned and pulled out his keys and stood, opening the door before they started to run again towards her door, knocking. With no answer, Charlie slipped away and went to open his door and ask Frank if he had seen Y/N. The door swung open revealing the pair laughing together drinking beer and Charlie smiled at them "Heyyy," Dennis rushed over to join Charlie. 

Y/N smiled, buzzed. "Hey" she gestured for them to sit with them. Charlie went to sit with her and she wrapped her arms around him, pulling him in. Dennis glared at Charlie but joined them watching the movie.

**Notes for the Chapter:**

> Stay safe and healthy guys, I love you all!


End file.
